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Q8.15(i):
How will you bring about the following conversion in not more than two steps? (i) Propanone to Propene

Solution :

Step 1: Reduction of Propanone to Propan-2-ol

The transformation of propanone ($CH_3COCH_3$) to propene requires a two-stage process: reduction of the carbonyl group to an alcohol, followed by dehydration. In the first step, propanone is treated with a reducing agent such as Sodium Borohydride ($NaBH_4$) or Lithium Aluminium Hydride ($LiAlH_4$).

Reaction:
$CH_3COCH_3 + 2[H] \xrightarrow{NaBH_4 / CH_3OH} CH_3CH(OH)CH_3$

Justification: [Per the mechanism of nucleophilic addition of hydride ions to the carbonyl carbon, the ketone is converted into a secondary alcohol].

Step 2: Dehydration of Propan-2-ol to Propene

The secondary alcohol (propan-2-ol) is subsequently subjected to acid-catalyzed dehydration using concentrated sulfuric acid ($H_2SO_4$) at $443 \, K$.

Reaction:
$CH_3CH(OH)CH_3 \xrightarrow{conc. H_2SO_4, 443 K} CH_3CH=CH_2 + H_2O$

Justification: [By Saytzeff's Rule and the mechanism of E1 elimination, the protonation of the hydroxyl group followed by the loss of a water molecule creates a carbocation intermediate, leading to the formation of the most substituted alkene].

Visual Representation of Molecular Transformation

Propanone NaBH4 Propan-2-ol H2SO4, Δ Propene
Reagent Step Resulting Compound
$NaBH_4$ 1 Propan-2-ol
Conc. $H_2SO_4$ 2 Propene

Final Solution: The conversion of propanone to propene is achieved in two steps: first, reduction of propanone using $NaBH_4$ to propan-2-ol, and second, acid-catalyzed dehydration of propan-2-ol using concentrated $H_2SO_4$ at $443 \, K$ to yield propene.


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